After nearly a decade of groundwork, Minneapolis, Minnesota emcee/singer/author and Dessa is breaking into the mainstream. This month she concluded her first headlining national tour after scoring a Top 200 debut for her latest album, Castor, The Twin. The work reinterprets some previous works from Dessa’s vast solo catalog, which dates back to 2005’s False Hopes.

With her Doomtree brethren P.O.S., Cecil Otter, Sims and others, Dessa released the group album No Kings earlier this week. The collective’s first album since 2008’s self-titled release is a milestone for the indie stalwarts.

Before her show earlier this month in Philadelphia, Dessa sat in a crowded Market Street cheese-steak eatery with HipHopDX and discussed this new solo album, No Kings and her relationship with Hip Hop.

Dessa: I don’t write with other eras in mind, but I will say that probably naturally, my tastes tend to align with zeitgeist that are maybe now a little out of fashion. So I dig irony, but with a gentler touch than I think has been popular since the ’90s. So I’m into the pre-war idea of not…a sensitive sensibility [but earnestness]. I dig that…post-modernists say it’s an ironic sensibility, that earnestness is more regulated to the war and before when people were feeling things so enormously that they didn’t make any jokes about them. I think probably now we’re kinda more winking and we have nostalgia for 15 years ago. And I dig some of that stuff as a consumer but not as an artist really.

DX: With this album, you’re re-presenting these songs for the most part. I’m curious to know for you, what did that feel like? I talk to a lot of artists who refer to songs like their babies…How was it for you to choose songs and not the others? And still make a cohesive project?

Dessa: I think there were two criteria by which I was selecting songs for inclusion on: one was, the degree of difference between the original recording and the live instrumentation recording. For example, “The Chaconne” is probably the most similar of the 12 songs on [Castor, The Twin] to the original. More similar than that… We had some tunes that feature organic instrumentation, originally. So to voice them organically didn’t make for a really big aesthetic switch. While I enjoyed playing those, it didn’t seem worth re-recording. We’re looking for songs that were aggressively re-arranged so that they really do sound like new – same lyrics, the same chords but really being viewed from a very different feeling. Like scenes of a different vantage point. And then, the second criteria was generally how successful is the song translated on organic instruments. I think they are one or two tunes that didn’t make that leap quite as well as the others did. It was a little bit hard to axe them. But listening to them in headphones, in sequence I thought that this is obviously the orphan.

DX: The easiest most tangible example I can think of is Eric Clapton’s song “Layla.” When he first did it, it had a different tone or meaning than when he did it later, acoustically. Both times it was very popular. Did you feel anything like that, where the songs took on different meaning?

Dessa: A couple of them did. I think “Palace” was a song when I initially recorded that did seem kind of timely. It was a lighter song but it wasn’t a party drag.

DX: Congratulations. You made the Top 200 with Castor, The Twin. I’m sure it’s weird to talk about commercial success. But how does it feel to really break into the mainstream?

Dessa: I think the approach has worked for Doomtree. That approach is just really slow. It’s like trying to build a label through a chain letter, it’s just slow to spread. Even if everybody does their parts and tell their friends, there’s this kind of exponential growth curve which stays flat for a long time before it starts pulling up and becoming something closer to vertical lines. It’s been five, six, seven, eight years tryin’ to make it and its felt like there was kind of a critical mass. I dont want to overstate our current position. But it was a big deal to get most of us to quit our day jobs to just focus on music. That’s obviously an easy benchmark. That probably is the one that means the most to most of us – being able to spend your life the way you want to spend it.

DX: In 2011, independents are winning. From Tech N9ne, Mac Miller, Murs, Atmosphere, do you think authenticity has leveled the playing field?

Dessa: I do. And I think that the first-person nature of Hip Hop has always valued authenticity. We always get suspicious or salty or mad when we find out that someone is telling a story in the first-person with what we believe is autobiographical details, and then find out that…was an act of fiction instead of saying “Oh, that’s fiction!” It’s not what we really understand Rap music to be. The default is true stories where we expect it to be true unless you tell us they’re not. Or unless you give us some obvious indicator that they’re not. So yeah, I think people do value that authenticity. People want it to be real, they want it to be true.

DX: In your live shows, how much does the set-list feed off the crowd? Does your set-list change?

Dessa: I think for tonight, a lot. ‘Cause we played yesterday in Arlington and my set was a lot of fun. But my actual set order kinda sucked. So I wont be doing that one again.

DX: Do you switch it up from night to night being on tour so much?

Dessa: I will. If we land on something that seems to really work, I’ll still make changes but minor ones. So we’ll kinda have a template where we can make some revisions. But last night’s wasn’t our best. It was a lot of fun to perform but it took a lot of explaining to the crowd like “Now, we’re doing a ballad!” You know? It was joke but we’re willing to go there. Like “Let’s suffer through this set-list guys but we got this!” But it kinda depends on the room sometimes. I’m so learning that since its my first performance in front of a lot of people so it’s like, you know, when you meet the parents the first day you straighten your tie, because you’re trying to make an impression. And then when you’re there for Christmas, you come and pet the dog and make the same old jokes, and you know, there’s a degree of formality but your character has already been established. I been playing for crowds that have known me for awhile. So now it’s a good exercise to be re-introducing myself again to crowds.

DX: What is it about Minneapolis artists. You have Bob Dylan, The Replacements, The Holdsteady, Atmosphere, Prince, Doomtree. Is there a common thread?

Dessa: You know, it’s a question we get a lot so I should have come up with a better answer by now but I think sometimes it feels like being asked “What was it like to grow up with your mom and your dad?” And it’s so hard to get enough perspective without getting a Psychology degree first to be able to meaningfully compare where you grew up to other places you did not grow up, you know? So I almost feel like the boyfriend, and the girlfriend sometimes has a better perspective [as a witness]. I’ll tell you what is like growing up with his mother…so I grew up there for the entirety of my childhood and adolescence for the most part, and I don’t know, I’m not sure. I was a really studious kid and kind of a loner and I didn’t realize we had a music scene until I…before doing shows, I was very much so a bookworm. I missed it I think. I don’t know. It’s awesome and I recognize it but I’m not a credible commentator on why. I think something feels a little scrappy about it. It’s like a welter-weight fighting out of its class or has something to prove. And maybe it’s ’cause we don’t have talent-scouts, nobody is gonna come and save you from your career and if you’re gonna do something, you’re gonna do it yourself. Or you’re gonna hire a friend. And pay him with drink tickets to get it done. I think there is that sort of like “Yeah, I know you think I’m from; I got something to prove to you.” That kind of feel to it, yeah.

Dessa Explains Recording No Kings With Doomtree

DX: How was it recording No Kings with Doomtree, after you’ve all found so much solo success and identity in the last several years?

Dessa: I think to some extent we were all a little bit more comfortable with our voice. You know, when I started rapping, you’re apprehensive about what people are gonna think. And am i supposed to sound more like so and so and um, after a few years, some kind words have been said to you and some critical words have been said to you, and you’re gonna decide that when you follow your own vision, you’re gonna take some hits and I think most of us are really willing to bring our best in our most authentic selves, understanding that we have the virtue of having worked with each other for eight or nine years… there will be some cohesion there. And if we really are five different voices, and um…to make it we…so we kinda locked ourselves in a cabin without Internet or our cell-phones and played beats. None of us came with song ideas, none of us came with lyrics we had our beats already…and we just played them on repeat wrote all day, demoed until the morning hours and did it again the next day.

DX: Was that fun?

Dessa: Everyone would say yes, and I would nod quietly in the corner. It was hard. It was meaningful, it was satisfying, it was gratifying, but fuck…I don’t know, that’s not my idea of kickin’ back. I don’t know if it was fun but it felt like the right thing to do. And I’m really glad we did it. If that makes sense. I get weird and cerebral when I’m writing so it’s not something I love doing with other people to watch me freak out.

DX: What’s your relationship like with Hip Hop and Rap music…where is it at right now?

Dessa: I think its something I try not to think too hard about, ’cause it is a complicated relationship, you know? For as much Rap music that moves me, I don’t think that Rap’s reputation as misogynistic or violent is unearned. I think that it is overplayed and that it is. Sometimes it feels like a very small sample group makes an impression for a vast range of music – for what I think of what Hip Hop is doing culturally; at least the really flagship artists. With that said, as a musician, you know, a lot of times… is this Rap, is this songwriter stuff, is this Indie stuff, is this a Jazz record? And I think those are useful terms to talk about music but I don’t think they’re useful terms to make music. You know? And rapping and singing doesn’t feel that different to me. And it seems unlikely if I chose to get a lil more singy-er… then all of a sudden this is a different genre… but I just sang a few notes and then I’m going back to how I was delivering it. Like, did I really just cross some vast partition…not to say that “I’m not in any genre, you can’t tie me down!” but I say that only ’cause it has helped me make better music.

DX: When you’re on tour, i know everyone’s daily routine is different but when you poke your head in record stores, are you ever shocked to see your work put in different sections?

Dessa: You know, so far because of the Doomtree connection it’s always in Hip Hop but I think probably the biggest suprise is when someone picks it up and goes “What the hell is this?!” The surprise is probably from the consumer end. But because of my history, it’s almost aways shelved in Hip Hop, yeah.

DX: What’s the proudest verse of your career?

Dessa: The last verse of a song called “Annabelle,” which is not released yet on record.